The role of terphenyl-containing carboxylic acid in the oligomerization of aryl vinyl ketone

The molecular structure of 8-((4′′-((1 R ,4 S )-4-butylcyclohexyl)-2′-chloro-[1,1′,4′,1′′-terphenyl]-4-yl)oxy)oct-1- en -3-one (TERPh-VK) and 6-((4′′-((1 R ,4 S )-4-butylcyclohexyl)-2′-chloro-[1,1′:4′,1′′-terphenyl]-4-yl)oxy) hexanoic acid (TERPh-COOH) is analyzed by FTIR spectroscopy. Vinyl ketone isolated from solution forms a thermodynamically unstable cis conformation due to probable peculiarities of the crystal structure formation. The heating of this substance above 100 °C results in the cis - trans transformation with the simultaneous opening of the vinyl double bond. The mixing of the above terphenyls in solution followed by the isolation of the solid product results in the formation of the TERPh-VK/TERPH-COOH associated species due to the H-bonding between ketone and carboxylic groups. The thermal transformation of the H-bond associated species resulted in the formation of the oligo (TERPh-VK)/TERPh-COOH associated species. 8-((4′′-((1 R ,4 S )-4-butylcyclohexyl)-2′-chloro-[1,1′,4′,1′′-terphenyl]-4-yl)oxy)oct-1- en -3-one (TERPh-VK) and 6-((4′′-((1 R ,4 S )-4-butylcyclohexyl)-2′-chloro-[1,1′:4′,1′′-terphenyl]-4-yl)oxy) hexanoic acid (TERPh-COOH) are, analyzed by FTIR spectroscopy.